2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 50907190, compound

HRID 1431397Notes

Reaction equation

HRID 1431397 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[O:35]1[CH2:40][CH2:39][N:38]([C:41]2[CH:47]=[CH:46][C:45]([N:48]3[CH2:53][CH2:52][O:51][CH2:50][CH2:49]3)=[CH:44][C:42]=2[NH2:43])[CH2:37][CH2:36]1.Cl[C:55]1[C:64]2[C:59](=[C:60]([C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][N:66]=3)[CH:61]=[CH:62][CH:63]=2)[N:58]=[C:57]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][N:72]=2)[C:56]=1[CH3:77].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:38]1([C:41]2[CH:47]=[CH:46][C:45]([N:48]3[CH2:49][CH2:50][O:51][CH2:52][CH2:53]3)=[CH:44][C:42]=2[NH:43][C:55]2[C:64]3[C:59](=[C:60]([C:65]4[CH:70]=[CH:69][CH:68]=[CH:67][N:66]=4)[CH:61]=[CH:62][CH:63]=3)[N:58]=[C:57]([C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][N:72]=3)[C:56]=2[CH3:77])[CH2:39][CH2:40][O:35][CH2:36][CH2:37]1

Participants

8

Reactant 4

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 288098152,5-DimorpholinobenzenamineHCID 59631221HCID 59631221, compound

Product 1

HCID 50907190HCID 50907190, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.023 g, 0.048 mmol), 2,5-dimorpholinoaniline (0.095 g, 0.36 mmol), 4-chloro-3-methyl-2,8-di(pyridin-2-yl)quinoline (0.1 g, 0.30 mmol) and Pd2dba3 (0.011 g, 0.012 mmol) in toluene (3.00 mL) was added sodium tert-butoxide (0.072 g, 0.753 mmol). The reaction mixture was heated to 120° C. and stirred for 45 min. The reaction was then cooled to rt and diluted with water (25 mL). The mixture was extracted with EtOAc (2×10 mL) and DCM (1×10 mL). The organic layers were combined and washed with brine (1×20 mL) and dried over magnesium sulfate. The crude product was purified by column chromatography on basic alumina (0 to 50% EtOAc in hexane) to give the desired product N-(2,5-di(4-morpholinyl)phenyl)-3-methyl-2,8-di(2-pyridinyl)-4-quinolinamine. 1H NMR (400 MHz, CDCl3) δ ppm 8.78 (1H, d, J=4.1 Hz), 8.69 (1H, m), 8.30 (1H, m), 8.20 (1H, m), 7.96 (2H, m), 7.80 (2H, m), 7.59 (1H, dd, J=8.3, 7.3 Hz), 7.32 (2H, m), 7.10 (1H, m), 6.43 (1H, m), 6.03 (1H, br. s), 3.92 (4H, br. s), 3.71 (4H, br. s), 3.08 (4H, br. s), 2.91 (4H, br. s), 2.53 (3H, s). Mass Spectrum (ESI) m/e=559.3 (M+1).

Workup

  1. temperatureThe reaction was then cooled to rt
  2. extractionThe mixture was extracted with EtOAc (2×10 mL) and DCM (1×10 mL)
  3. washwashed with brine (1×20 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe crude product was purified by column chromatography on basic alumina (0 to 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-4d1483419e0d4c379bed8e6199046ead
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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